Method of making alkali metal salts of organosiloxanols and organosilanetriols



Patented Mar. 4, 1952 UNITED STATESPATENT OFFICE METHOD OF MAKINGALKALIMETAL SALTS OF ORGANOSILOXANOLS AND ORGANO- SILANETRIOLS Clinton W.MacMullen, Fayetteville, N. Y., as-

signor to Cowles Chemical Company, Cleveland, Ohio, a corporation ofOhio No-Drawing. Application December 31, 1948, Serial No.- 68,750

This invention relates to organosilicon compounds and compositionscontaining the same. More particularly the invention relates to a novelclass of compounds comprising salts, particularly water-soluble metalsalts, of organosilane-;

triols, mono-organosiloxanols and mixtures of these compounds. The termmono-organo is used in the present specification and claims to designateorganosilicon compounds wherein each silicon atom has a single organicsubstituent thereon.

This application is a continuation-.in-part of my prior applicationSerial No. 782,683, filed October 28, 1947, now abandoned. The claims ofthe present application are directed to com-- -materialswater-repellent. I have now discovered another class or organosiliconcompounds which possess a number of interesting and useful propertiesquite different from the properties of the silicones and which arereadily convertible into silicones and may, as indicated hereafter, beused with advantage as silicone-forming compositions. More particularlyI have found that metal salts of organosilanetriols,mono-organosiloxanols, and mixtures thereof may be prepared in aqueoussolution and when properly so prepared they reduce markedly the surfacetension of the solution, enhance its wetting properties, and conferdetergent properties on the solution. Moreover these solutions, whenacidified or diluted with water and preferably heated, produce siliconepolymers and hence they may be used as siliconeforming compositions incases where it may be desirable to deposit silicones in situ inrelatively inaccessible locations. For example, the solu-' tions of thepresent invention, because oftheir low surface tension and wettingproperties, easily wet and penetrate the fibers ofa fabric and when thefabric has been thoroughly wetted with sucha solution it may beacidified to precipitatea silicone polymer on the surfaces and in thecapillaries of the fibers of the fabric, thus 7 Claims. (01. zen-448.2)

producing a durable, resistant and water-repellent protective coatingonthe fibers. The compounds of the present invention-in- ,clude both theorganosilanetriols and the monoorganosiloxanols and may be representedbythe following general formula which is genericto these two groups ofcompounds:

[(R Si) n+102n+31mMn+3 In this formula R. is an organic substituentselected from the group consisting of aryl, alkaryl, aralkyl, andalkylaralkyl radicals, nis selected from zero and the positive integers,M is a metal or strong organic base and m is an integer representing thevalence of M. In cases where a water-soluble product is desired M ispreferably an alkali metal or it may also be a quaternary ammoniumradical. In such a case the above formula may be written:

[ (R Si) n+10w] (O M) n+3 It will be recognized that there are twoprincipal groups of compounds comprehended within this general formula,which groups may be called respectively mono-organosilanetriolates andmono-organosiloxanolates and which may be represented by the followinggeneral formulae wherein M is monovalent:

silanetriolates R Si (OM):

OM OM 0M I I Siloxanolates MO-At-O-Si-O Si-OM The silanetriolates may beconsidered monomers and the siloxanolates polymers. The-sil oxanolatesmay exist as linear, cyclic or crosslinked polymers and mixtures of suchpolymers.

The compounds of the present invention may be prepared by a variety ofmethods, several of which are described hereafter. In many cases it isconvenient to prepare the compounds in aqueous solution both becausethey are customarily used in aqueous solution and because they arestabilized against hydrolysis and condensation by the presence ofalkali. As indicated hereafter the compounds may also be prepared as drysolids. In accordance with a preferred method, the present compounds areprepared by hydrolyzing in aqueous alkali solution an organoto thewell-known Grignard reaction. vIn general,

the hydrolysis reaction may be carried out by preparing an aqueoussolution of an alkali and adding the organotrihalosilane in solution ina suitable solvent to the aqueous alkali with vigorous stirring.Thehyd'rolysis proceeds easily and rapidly to give "an aqueous solutionof the desired product. In general the hydrolyzing solution shouldcontain at least six equivalents of alkali per mol of trihalosilane.

The concentration of caustic alkali'in the hydrolyzing solution may varyfrom about 5% to about 35% by weight, although in particular cases thehydrolysis may be effected with caustic alkali solutions more dilutethan 5% and more concentrated than 35%.

In order to point out more fully'the nature of the present invention,the following specific examples are given to illustrate certaincompounds falling within the scope of the invention and the manner inwhich they may be prepared. It is to be understood that the followingexamples are illustrative only and it will be apparent to thoseskilledin the art that numerous other compounds may be'prepared and thatthe illustrative meth- UdsEdes'ctib'ed may be modifiedin various ways toadapt the methods andcompounds to particular uses.

Example 1-.-An aqueous solution of sodium hydroxide was prepared bydissolving 47.1 grams of sodium'hydroxidein'zti'lcc. ofjwater. 'To this"sodium hydroxide solution a solutionof '15 grams or "methylphenyltrichlorosilane in 100 cc. of petroleumiether'having a boiling point of30 C. :to65C. added. The sodium hydroxide solution was'agitated during"the addition of methylphnyltrichlorosilane solution, and the methyl-.plfenyltrichlorosilane solution was added over a "period ofapproximately five minutes. The resulting mixture was agitated for aperiod of about A; an hour to produce the sodium salts of themethylphenyl trichlorosilane hydrolysis products, and it was noted thatconsiderable foam developed during "this agitation. The petroleum ether-evaporated off during the agitation period. 'When "the agitation wasstopped the foam subsided audit was noted that a small amount of"insoluble material had been formed. This insoluble material was removedby filtration and the filtered solution analyzed.

Analysis showed that the solution contained about -2.3:% by weight ofsodium methylphenyl compounds. The surface tension of the solution was3'7 dynes per centimeter as compared to 65 dynes per centimeter for acaustic soda solution of the same NaOI-I content.

'Eaam'pZe 2.-A solution of 20 grams of ethyl- K phenyl trichlorosilanein anhydrous ethyl ether was added to a solution of 166 grams of causticsoda in l'494 cc.'of water during a'p'erio'd of about "fiv'e'minuteswith vigorous stirring. The mixture was stirred for about four hours andappeared turbid "due to *a suspension of oil. The solution was filteredto remove a "small amount of gelatinous precipitate.

Analysis indicated that the solution contained about 1.4% of the sodiumethylphenyl compounds. The'sur'facetension of the solution was '34dyn'e's per centimeter as compared to 51 dynes per-"centimeter for acaustic soda solution of the sameNaUI-Ico'ntent, 'and'thus the surfacetension of the solution was lowered appreciably by the presence of thesodium ethylphenyl compounds. AI solution containing 1% of the sodiumethylphenyl'compounds'andl i'fi, NaOI-Iwetout cottonsk'einsintenminiites by the Braves testas compared to 69 minutes for a14% NaOH solution alone.

Example 3.-A solution of 15 grams of isopropylphenyl trichlorosilane incc. of petroleum ether was prepared and added to a caustic soda solutionmade by-dissolving40 grams of sodium hydroxide in 236 cc. of Water. Theisopropylphenyl trichlorosilane solution was added to the caustic sodasolution over a period of five minutes with stirring and the resultingmixture agitated for three hours during which time the petroleum etherevaporated and foam developed.

It was observedfthat a small amount of insoluble material was formed andthis insoluble material was removed by filtration and the solutionanalyzed. Analysis showed that the solution contained about 1.4% byweight of the sodium isopropylphenyl compounds and the surface tensionof the solution was 41 dynes per centimeter as compared to 6'7 dynes percentimeter for a sodium hydroxide of the same NaOH content.

Example T4.A:'solution of 15 gramsof di-iso- 'propylphenyltrichlorosilane in 100 cc. of petroleum ether was'prepared and added toa caustic soda solution made by dissolving 35.4 grams of sodiumhydroxide in 200 cc.*of water. The diisopropylphenyl trichlorosilanesolution was added to the sodium hydroxide solution over a periodfoffive minutes with "stirring. The resulting-mixture was allowed to standfor a period of eight days with intermittent stirring, then-diluted with50- cc.'of "water and filtered.

Analysis of the filtered solution showed that it contained about 1% ofthe'sodium di-isopropyl- .phenyl'comp'ounds'a'nd the surface tension ofthe solution was '33 dynes per centimeter as compared .to 52 dynes :percentimeter 'for a caustic soda solution "of the same "Na-OH content.

Example 5.A solution of 15 grams of butyl- *phenyl 'trichlorosilane in'100 cc. of petroleum ether was prepared and added to a caustic sodasolution made by dissolving 39.7 grams of sodium lhydroxi'de'in 225 'cc.of water. The 'two'solutions were mixed over a period of five minuteswith stirring. After addition 'of the butylphenyl trichlorosilanesolution had been completed, the mixturewas stirred'for one hour duringwhich time considerable foam developed and the'mixture was then allowedto stand for several days and filtered.

Analysis of 'thetfiltere'd solution showed that it 'c'ontained'about2.8% of the soluble sodium butyl- *phenyl compounds. The surface tensionof the solution was 42 dynes per centimeter as compared to '70 dynes percentimeter for a sodium hydroxide solution of the same NaOI-I content.

Example 6.--Fifteen grams of amylphenyl tri- -chlorosilane in 100cc. ofligroin were added dropwise with stirring "to a caustic potash solutioncomprising 117 grams of 'KOI-I in 234 cc. of Water. The'hydrolysisreaction evolved considerable heat causing about half of the ligroin tobe distilled off. The reaction mixture was steam distilled for aboutfive hours to remove the remainder of the ligroin and-a considerableamount of foam was produced during this period. A quantity of awhiteprecipitate was formed which was filtered offrand the filteredsolution was analyzed.

Analysis showed that the solution contained about 2.1% of the potassiumamylphenyl compound. The mol ratio of potassium to silicon was 1.0: 1,indicating that the product was a cyclic polymer. The surface tension ofa-solution containing 1% of th'e'potassium 'amylphenyl compoundtogetherwith 9 potassium hydroxide was about 45 dynes per centimeter as comparedto 58 dynes per centimeter for a potassium hydroxide solution of thesame KOH content, thus indicating that the potassium amylphenyl compoundreduced the surface tension of the solution appreciably.

Example 7 .-A solution of grams of diamylphenyl trichlorosilane in 100cc. of petroleum ether was added to a caustic soda solution made bydissolving 30 grams of sodium hydroxide in 185 cc. of water. Thediamylphenyl trichlorosilane solution was added to the sodium hydroxidesolution over a period of three minutes with agitation. It was observedthat the viscosity of the solution increased in the course of thehydrolysis reaction. After completion of the reaction the solution wasfiltered and the resulting filtered so"- lution had a surface tension of47 dynes per centimeter.-

Example 8.A solution of 18.9 grams of amylnaphthyl trichlorosilane in100 cc. of dry ethyl ether was'prepared and added to a solution ofcaustic soda made by dissolving 150 grams of sodium hydroxide in 850 cc.of water. The amylnaphthyl trichlorosilane solution was added'to thesodium hydroxide solution over a period'of five minutes with agitation,and the agitation continued for about four hours thereafter. Theresulting product was allowed to stand over night, then agitated a fewmore hours and filtered.

Analysis of the filtered product showed that it contained 0.6% of thesodium amylnaphthyl compounds and the surface tension of the solutionwas 34 dynes per centimeter as compared to 52 dynes per centimeter for asodium hydroxide solution of the same NaOH content.

Example 9.A solution of 15 grams of tetrahydronaphthyl trichlorosilanein 100 cc. of ethyl ether anhydrous was added to a solution of 75 gramsof sodium hydroxide in 425 cc. of water during five minutes withvigorous stirring. Appreciable foam developed during a period of threehours of stirring.

Analysis indicated that the solution contained about 2% of the sodiumtetrahydronaphthyl compounds and the Na:Si mol ratio indicated that thesodium tetrahydronaphthyl compound was substantially all present in themonomeric form. The surface tension of the solution was 46 dynes percentimeter as compared to 59 dynes .-'1 per centimeter for a causticsoda solution of the same NaOH content. The Draves test indicated thatcotton yarn was wet out more rapidly by caustic soda solution if 1% ofthe organosilicon compound was present.

trichlorosilane in ligroin was added to a potassium hydroxide solutioncomprising 40.8 grams of KOH in 200 cc. of water. The reaction mixturewas heated and stirred for a period of about 30 minutes and the ligrointhen removed by steam distillation over a period of about minutes.Foaming occurred towards the end of the distillation. The surfacetension of the resulting solution diluted to 10% total solids was 41dynes per centimeter as compared with a surface tension of about 59dynes per centimeter for a potassium hydroxide solution of the same KOHcontent.

:55 Example 10.--A solution of 6.1 grams of benzyl vigorous agitation.Thereafter the mixture was stirred for four hours, allowed to stand overnight and filtered.

Analysis of the filtered solution showed that it contained about 7.5% ofthe sodium methylbenzyl compounds and the surface tension of thesolution was 37.7 dynes per centimeter as com,- pared to 52.5 dynes percentimeter for a sodium hydroxide solution of the same NaOH content.

Example 12.A solution of 15 grams of ethylbenzyl trichlorosilane in 100cc. of petroleum ether was prepared and added to a solution of causticsoda made by dissolving 40 grams of sodium hydroxide in 226 cc. ofwater. Mixing of the solutions was effected over a'period of minuteswith agitation. The resulting foamy solution was stirred for severalhours, allowed to stand three days and filtered.

Analysis of the filtered solution showed that it contained about 1.8% ofthe sodium ethylbenzyl compounds and the surface tension of the solutionwas 36.5 dynes per centimeter as compared to 52.5 dynes per centimeterfor a sodium hydroxide solution of the same NaOH content.

Example 13.-A solution of 15 grams of diethylbenzyl trichlorosilane in200 cc. of petroleum ether was prepared and added to a caustic sodasolution made by dissolving 17 grams of sodium hydroxide in 154 cc. ofwater. Mixing of the two solutions was effected over a period of fiveminutes with vigorous agitation. The resulting mixture was stirred forthree hours and after standing over night was filtered.

Analysis of the filtered solution indicated the presence of about 1 ofthe sodium diethylbenzyl compounds and the surface tension of thesolution was 34 dynes per centimeter as compared to 52.5 dynes percentimeter for a sodium hydroxide solution of the sameNaOH content.

Example 14.-A solution of 15 grams of amylbenzyl trichlorosilane in 100cc. of petroleum ether was hydrolyzed with a solution comprising 623grams of KOH dissolved in 478 cc. of water. The procedure of Example 1was followed and the product solution analyzed.

The anaylsis showed that the solution contained about 2.8% of thepotassium amylbenzyl compounds and the mol ratio of potassium to siliconindicated that the potassium amylbenzyl compound was present in the formof polymeric chains having some cross-linking. The surface tension ofthe solution was dynes per centimeter as compared to 59 dynes percentimeter for a potassium hydroxide solution of the same KOH content,and thus the potassium amylbenzyl compound reduced the surface tensionof the solution appreciably. A solution containing Example 11.A solutionof 15 grams of meth- .ylbenz'yl trichlorosilane in 200 cc. of petroleumether was prepared and added to a caustic soda solution containing 25grams of sodium hydroxide-M 227 cc. of water. The methylbenzyltrichlorosilane solution was added to the sodium hydroxide solution overa period of 30 minutes with 1% of the potassium amylbenzyl compound and20% potassium hydroxide wet out cotton skeins in seven minutes by theDraves test.

Example 15.- A solution of 15 grams of isopropyl-phenyl-ethyltrichlorosilane (i-csm-cem-cmcmsich) in 200 cc. of petroleum ether wasprepared and added to a caustic soda solution made by dissolving 21.4grams of sodium hydroxide in 193 cc. of water. Mixing was effected overa period of 20 minutes with agitation and the agitation continued forseveral hours. The solution was permitted to stand overnight andfiltered.

Analysis of the filtered solution showed the presence of about 1% of thesodium isopropylphenyl-ethyl compounds and the filtered solution had asurface tension of 28.5 dynes per centimeter .7 as compared to 52 .dynesper centimeter for a sodium .hydroxide -1S01l1tl0l'l f the same 'NaOI-Icontent. The mol ratio of sodium to silicon in this product indicatedthat the product was a mixture of the monomer and dimer.

"The foregoing examplesillustrate methods of preparing salts of themono-organosilanetriols and *mono-organosiloxanols in aqueous solution.Asiindicated above'it is also possible to prepare thesesalts insolid"form and the following examples illustrate methods .of preparing thesolid salts.

Example 16.--A =flask was charged with five grams of zphenyltrichlorosilane and about 150 cc. of concentrated ammonium hydroxide wasadded slowly. White fumes of ammonium chlo ride were given off and awhite precipitate "was formed. The excess ammonium hydroxide solutionwasremoved by Tdecantation and the remainingprecipitate dissolved in about50 "cc. of ethyl ether. 6.5 grams of 'solid'KOl-I was then added totheether solution with vigorous shaking, ammonia and ether fumes were"given oil and a white precipitate formed. Ether was decanted from thewhite precipitate which was then dried in vacuo and recrystallized fromethy1 alcohol. "Analysis of the crystals showed a mol ratio of potassiumto silicon of about 1.4 to 1, indicating that the product was a mixtureof polymers having an average size of five silicon units. Thepotassiumphenyl compound was soluble in dilute alkaline solutions andlowered the surface tension of them.

Example 17.-A flask "was charged with 56.3

grams of benzyl trichlorosilane and 150 cc. of concentrated ammoniumhydroxide was added slowly. The reaction proceeded with considerableviolence, fumes of ammonium chloride were given off, and a whiteprecipitate was formed. Excess ammonium hydroxide solution was re movedby decantation and the precipitate dissolved in'200 cc. of ethyl ether.56.1 grams of solidcaustic potash was then added to the ether solutionwith vigorous shaking and a white precipitate was formed and ammoniafumes were given off. The precipitate was recrystallized from ethylalcohol several times and 'yielded clear transparent needle-likecrystals. Analysis of the crystals showed a mol ratio of potassium tosilicon of about 2.4:1, thus indicating that the product was a mixtureof the monomer and dimer. The crystals were water-soluble aand when'dissolved in dilute caustic potash solution reduced the surface tensionof the resulting 'solution.

Example 18.A reaction "flask was charged with approximately 200 cc. ofliquid ammonia. A solution-of '15 grams of amylphenyltrichlorosilane in100 cc. of anhydrous ether was "added dropwise'to the liquid ammonia andheavy ammonium chloride fumes were given off as the reaction proceeded.When the addition of the amylphenyl trichlorosilane was complete, asolution of 8.9 grams of potassium hydroxide in B0 cc. of anhydrousethyl alcohol was added and the mixture agitated and allowed to standfor seven days. An additional grams of potassium hydroxide dissolved-in50 cc. of anhydrous "ethyl'alcohol was'then added and the mixturefiltered. The resulting alcoholic solution was set in a desiccator for"a period off-thirty days 'fd'urin g wh'ich'time about 10 grams' ofcrystals were-formed which were washed and dried.

It 'wasifound that'these crystals were soluble in dilute caustic potashsolution .and that they reducedthe surface tension of a5%KOH-solution'from 60 to :31.dynes per centimeter when present to theextent of about 1% :by weight in the solution. The mol ratio ofpotassium to silicon in this crystalline product was about 2.111, thusindicating that the compound :was present in both-polymeric andmonomeric form.

Example 19.-A solution of 104.? grams of potassium acetate in 340 cc.glacial acetic acid was added to 50 grams of amylphenyl 'trichlorosilaneand an oily layer formed. The mixture was refluxed for about 'four hoursand after it had stood several days an oil layer was separated "whichcomprised amylphenyl silane-triol 'triaeetate. This silanetriol triesterwas saponified by trefluxingrfor about eight hours With-a solution of59.8.grams KOH in,150 .cc. anhydrous ethyl alcohol. The solution wasplaced 2111 'a desiccator'where crystallization took placeslowly during*a period of three weeks. The crystals were separated and analysis gavea mol ratio'of potassium to silicon of 2.6:1 indicating that thepotassium amylphenyl compound was present as a mixture of monomer anddimer. The crystals were soluble in dilute KOH solution and produced afoam.

Example 20.5.63 grams of amylphenyl trichlorosilane wasadded'dropwise'with stirring to a solution of 6.5 grams of KOH in50 cc.of anhydrous ethyl alcohol. The solution was decanted from theprecipitate of KCl and placed in a desiccatorfor about a month, and thecrystals :which formed were then separated by filtration and washed withethyl alcohol and ether. Analysis indicated thatcrystals of thepotassium amylphenyl compound were formed which were a mixture ofmonomer and dimer. The crystals were soluble in diluteKOI-I solution andproduced foam.

From the experiments that form the basis of the foregoing examples andalso from other experiments that I have performed, it'is possibleit'make certain general statements .con-

cerning the properties and characteristics of the products of thepresent invention. It appears that all of these products, whenincorporatedin aqueous solutions of alkali, cause the surface tensionsof the solutions to'be reduced below the surface tension valuesexhibited by caustic solutions of equivalent caustic concentration"which do not contain the compounds. The reduction in surface tensionvaries somewhat with the type of organic substituent in the product.

From the foregoing description it is apparent that the present inventionprovides a novel group of organosilicon products that are water andalkali-soluble and are capable of reducing the surface tension ofaqueous solutions. They have wetting and detergent properties and can beprecipitated from alkaline solution by reduction ofthealkalinity of thesolution, e. g. by diluting or .acidifying..the .solutioh, to formsilicone poly- -mers. Thus the solutionsmay be used as a medium forforming silicones indifiicultly accessible locations, as for example, inthe capillaries of and the interstices between the fibers of a fabric.Other applicationsof the present compounds and their aqueous andalkaline solutions will be apparent to those skilled in :the .art.

"Since many embodiments.:might';be made so! the present invention andsince many changes "might be made in the embodiment disclosed-herein,:it is tobe understood 'that the :foresoins description is to beinterpreted as illustrative only and not in a limiting sense.

I claim:

1. The method of making a surface active organo-silicon-containingreagent adapted to be used in the preparation of organo-silicon coatingswhich comprises causing an organo-trihalosilane, wherein the organoradical is selected from the group consistin of aryl, alkaryl, aralkyland alkylaralkyl, to react with an aqueous solution of an alkali metalhydroxide con taining at least six equivalents of said hydroxide per molof trihalosilane to form a water-soluble hydrolysis product of saidtrihalosilane.

2. The method of making a surface active organo-silicon-containingreagent adapted to be used in the preparation of organo-silicon coatingswhich comprises causing an alkaryl tri- I halosilane to react with anaqueous solution of an alkali metal hydroxide containing at least sixequivalents of said hydroxide per mol of trihalosilane to form awater-soluble hydrolysis product of said trihalosilane.

3. The method of making asurface active organo-silicon-containingreagent adapted to beused in the preparation of organo-silicon coat ingswhich comprises causing ethylphenyl-trichlorosilane to react with anaqueous solution of an alkali metal hydroxide containin at least sixequivalents of said hydroxide per mol of trichlorosilane to form awater-soluble hydrolysis product of said trichlorosilane.

4. The method of making a surface active organo-silicon-containingreagent adapted to be used in the preparation of organo-silicon coatingswhich comprises causing isopropylphenyltrichlorosilane to react with anaqueous solution of an alkali metal hydroxide containing at least sixequivalents of said hydroxide per mol of trichlorosilane to form awater-soluble hydrolysis product of said trichlorosilane.

5. The method of making a surface active organo-silicon-containingreagent adapted to be used in the preparation of organo-silicon coatingswhich comprises causing butylphenyl-tri chlorosilane to react with anaqueous solution of an alkali metal hydroxide containing at least sixequivalents of said hydroxide per mol of trichlorosilane to form awater-soluble hydrolysis product of said trichlorosilane.

6. The method of making a surface active organo-siliconcontainingreagent adapted to be used in the preparation of organo-silicon coatingswhich comprises causing amylphenyl-trichlorosilane to react with anaqueous solution of an alkali metal hydroxide containing at least sixequivalents of said hydroxide per mol of trichlorosilane to form awater-soluble hydrolysis product of said trichlorosilane.

7. The method of making a, surface active organo-silicon-containingreagent adapted to be used in the preparation of organo-silicon coatingswhich comprises causing di-isopropylphenyl-trichlorosilane to react withan aqueous solution of an alkali metal hydroxide containing at least sixequivalents of said hydroxide per mol of trichlorosilane to form awater-soluble hydrolysis product of said trichlorosilane.

CLINTON W. MACMULLEN.

REFERENCES CITED The following references are of record in the OTHERREFERENCES Meads et al., Jour. Chem. Soc. (London), vol. 107 (1915),pages 459-68.

Meads et al., Jour. Chem. Soc. (London), vol. (1914), pages 679-690.

1. THE METHOD OF MAKING A SURFACE ACTIVE ORGANO-SILICON-CONTAININGREAGENT ADAPTED TO BE USED IN THE PREPARATION OF ORGANO-SILICON COATINGSWHICH COMPRISES CAUSING AN ORGANO-TRIHALOSILANE, WHEREIN THE ORGANORADICAL IS SELECTED FROM THE GROUP CONSISTING OF ARYL, ALKARYL, ARALKYLAND ALKYLARALKYL, TO REACT WITH AN AQUEOUS SOLUTION OF AN ALKALI METALHYDROXIDE CONTAINING AT LEAST SIX EQUIVALENTS OF SAID HYDROXIDE PER MOLEOF TRIHALOSILANE TO FORM A WATER-SOLUBLE HYDROLYSIS PRODUCT OF SAIDTRIHALOSILANE.